This paper reflects on a case study in which a soft OR problem structuring approach, based on Soft Systems Methodology (SSM), was used to help in the design of an information system for health service users providing care in the community in a part of the South and West Health Region in the UK. The paper reflects on why an apparently 'successful' structuring led to an apparently 'unsuccessful' implementation. As part of this reflective process, the paper makes a contribution to the soft OR literature by reviewing some of the approaches taken in the literature to the evaluation of success of problem structuring using soft OR. This review reveals a lack of evaluative criteria, a lack of clarity over the identification of users, and a failure ...